Top Tech Jobs & Startup Jobs in Chicago, IL

The Business Development Representative will generate pipeline, qualify leads, close small deals, and collaborate with AEs in a high-caliber selling environment.

Responsible for maintaining and enhancing data warehouses and pipelines, developing scalable ETL processes, data analysis, and reporting through visualization tools like PowerBI.

The Staff Software Engineer will design and build scalable systems, lead architecture decisions, mentor engineers, and improve existing platforms using PHP, Node.JS, and AWS.

Design and build scalable backend components and indexing pipelines for semantic and hybrid retrieval, build retrieval orchestration and knowledge-graph services, improve retrieval quality via evaluation and observability, design APIs, and optimize latency, throughput, cost, reliability, and security for large-scale AI inference and retrieval workloads.

The Regional Sales Manager is responsible for driving new business and managing customer relationships in the transit tech sector, focusing on consultative selling and sales execution.

Manage employee questions and HR support, leaves of absence, benefits administration, HRIS operations, compliance, reporting, policies, and internal People Ops resources. Plan offsites, virtual events, and culture initiatives for remote and hybrid teams. The role partners with brokers, carriers, leave providers, and internal stakeholders while continuously improving processes and employee experience.

Own full-cycle, multi-state payroll for more than 1,000 employees using Rippling. Manage payroll tax accounts, filings, notices, reconciliations, audits, benefits, 401(k), workers’ compensation, year-end reporting, and payroll accounting. Serve as Rippling system owner, maintain payroll documentation, and build AI-enabled automation for payroll support, reporting, agency notices, and audit preparation.

Lead application security vulnerability management embedded with engineering teams, triage and fix vulnerabilities in a Clojure/JVM backend, operate cloud SecOps (SIEM/SOAR/CNAPP), perform security risk reviews and compliance support, maintain corporate workspace security, and mentor engineers on secure coding and secure defaults.

Lead and scale enablement programs across SDR, Sales, and Customer Growth teams. Build onboarding, continuous learning, playbooks, and enablement tech adoption. Define OKRs and measure ROI, partner with Product Marketing, and run workshops while shaping GTM and expansion motions.

Own Dispatch’s day-to-day legal function as a hands-on commercial attorney. Responsibilities include negotiating enterprise SaaS agreements, MSAs, order forms, DPAs, security addenda, privacy and data-sharing arrangements, employment agreements, vendor contracts, and other operational matters. The role partners with Sales, Product, Engineering, Security, Finance, People, and executives; builds scalable legal templates and playbooks; supports compliance processes; manages outside counsel; and establishes the legal infrastructure for company growth.